The Road to ILTACON 2026: Why Legal Tech Projects Need a New Playbook
ILTACON 2026 brings the legal technology community to the Gaylord Opryland in Nashville from August 23–27, 2026 for peer-driven education, practical programming, business partner conversations, and face-to-face networking. This blog continues Kraft Kennedy’s Road to ILTACON 2026 series, following Sulabh Upadhyaya’s look at what comes next for legal technology and Dan Paquette’s take on AI and Governance and legal tech’s next big test. Below, we shift the focus from emerging trends to the project leadership needed to turn those ideas into reality.
For greater insight into the upcoming conference, Beth Anne Stuebe sat down with Michael Walls, Practice Leader and Senior Project Manager at Kraft Kennedy, ahead of his ILTACON session, “Don’t Go Chasing Waterfalls: Project Leadership for Legal Tech.” The session will explore how legal technology leaders can guide complex initiatives through uncertainty, influence stakeholders without direct authority, balance agile ways of working with needed oversight, and define success by adoption and business impact rather than go-live alone.
Below are some of Mike’s insights: why traditional project models are being tested, where AI is changing the shape of legal technology delivery, and what firms may need most as they leave ILTACON and head into their next planning cycle.
From Linear Plans to Real-World Complexity
However, that is no longer the environment in which many legal technology teams are working. As Mike explained, the rise of AI and the growth of larger, more complex initiatives have introduced more unknowns into project delivery. Firms may begin with a clear plan, only to learn something during testing, user acceptance, or pilot phases that changes the direction of the work. Stakeholders may ask for a different approach. New requirements may emerge. A tool may behave differently in practice than it did in planning.
That does not mean structure is no longer necessary. It means project leaders need a model that can hold both structure and change at the same time.
Why Hybrid Project Leadership Matters
Mike sees more legal technology work moving toward a hybrid approach. Some phases can still be planned, scoped, and executed in a waterfall style. Initial planning, design, build, and configuration may follow a familiar path. But once a firm enters QA, UAT, pilot testing, or early adoption, the work often becomes more iterative.
At that point, teams may need to revisit configuration, adjust assumptions, refine requirements, and incorporate lessons learned from actual users. That is where agile thinking becomes useful, even when the project is not a traditional software development effort. Build a little. Test it. Learn from it. Adjust. Continue.
For CIOs, IT directors, project managers, innovation teams, and operational stakeholders, that shift has practical implications. Forecasting becomes harder. Resource alignment becomes more complex. Change management becomes inseparable from project management. And success depends on the ability to keep momentum without pretending that nothing will change.
AI Is Raising the Stakes for Project Management
AI is one of the clearest examples of why legal technology projects are becoming more fluid. Firms are not simply implementing a tool and moving on. They are trying to understand how AI fits into practice workflows, how attorneys and staff will use it, what governance should look like, how adoption should be measured, and whether the investment is producing real value.
Mike noted that AI is “the talk of the town” among the law firms he is working with, especially as firms evaluate tools such as Harvey, Legora, CoCounsel, Copilot, and Purview-related initiatives. The excitement is real, but so are the questions. Attorneys, paralegals, and other timekeepers may be energized by what AI can do, but firms still need to determine whether those tools are saving time, improving work quality, supporting business goals, and delivering a meaningful return on investment.
That is where project leadership becomes especially important. AI projects require governance, stakeholder alignment, realistic expectations, disciplined testing, strong communication, and a willingness to adapt as the organization learns. They also require a broader definition of success: not simply whether the tool went live, but whether people adopted it and whether the firm can point to measurable business impact.
What Firms May Need After ILTACON
Conferences like ILTACON often generate momentum. Leaders return home with new ideas, vendor conversations, peer insights, and pressure to act. The challenge is turning that energy into a portfolio of projects that can be prioritized, governed, staffed, and delivered.
For many firms, especially small and midsize organizations, the need may not be another tool. It may be project management capacity. Mike described two ways Kraft Kennedy helps firms meet that need. PMO as a Service helps clients establish governance, policies, procedures, and processes for turning initiatives into approved, budgeted, manageable projects. PM as a Service provides senior project management support for firms that may not be ready to build a full PMO but need experienced help managing a large portfolio of technology work.
Both models help legal technology leaders create control, visibility, and accountability. They can also serve as a proof of concept for firms that know they need stronger project management but are still making the case internally for a dedicated project management function.
Moving from Curiosity to Control
The legal technology landscape is not slowing down. AI, data governance, collaboration platforms, security requirements, mergers, integrations, and modernization initiatives are all competing for attention. The firms that make the most progress will not necessarily be the ones with the longest list of ideas. They will be the ones that can decide what matters, manage change thoughtfully, and guide projects to outcomes people will want to use.
And this is what is the heart of Mike’s ILTACON session: legal tech projects rarely move in straight lines anymore. His goal for the session is not to abandon structure or chase every change; it is to lead with enough discipline to stay accountable and enough flexibility to respond when the work reveals something new.
For firms, and friends, heading to Nashville, the question is not only what new technology they will discover at ILTACON. It is how they will turn the right ideas into projects that are governed well, adopted widely, and tied to real business value.
Ready to connect at ILTACON 2026?
Visit Kraft Kennedy’s ILTACON 2026 event page for registration details, agenda information, Golf Outing tickets, booth updates, featured session details, and much more.